Water → HCID 57377472, compound

HRID 1258915Notes

Reaction equation

HRID 1258915 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[N:14]=[CH:15][NH:16][CH:17]=3)=[C:11]([CH3:18])[N:10]=[N:9]2)=[CH:4][CH:3]=1.Cl[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[N:14]=[CH:15][N:16]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=4)[CH:17]=3)=[C:11]([CH3:18])[N:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 178434695HCID 178434695, compound

Product 1

HCID 57377472HCID 57377472, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(4-fluoro-phenyl)-5-(1H-imidazol-4-yl)-4-methyl-1H-[1,2,3]triazole (100 mg, 0.411 mmol), 2-chloro-5(trifluoromethyl)pyridine (75 mg, 0.411 mmol) and potassium carbonate (114 mg, 0.82 mmol) in DMF (2.0 mL) was stirred under Ar in a sealed flask and heated at 120° C. for 48 h. After cooling to room temperature the mixture was poured into water and the solid that formed was filtered off and purified by chromatography (silica, 0 to 100% ethyl acetate in heptane) to afford the title compound (98 mg, 60%) as a white solid. MS: m/e=389.2 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customthe solid that formed
  3. filtrationwas filtered off
  4. custompurified by chromatography (silica, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-f1d1704f638e4a7ca44a3546b6033707
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

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